


High School Reunion

by dirtydarkness418



Category: Gossip Girl
Genre: F/M, High School Reunion, M/M, Multi, Orgy, Slash, Smut, chair endgame, multiple sexual orientations, several OCs - Freeform, straight - Freeform
Language: English
Status: In-Progress
Published: 2017-09-27
Updated: 2017-09-27
Packaged: 2019-01-06 05:03:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,458
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12204411
Author URL: https://archiveofourown.org/users/dirtydarkness418/pseuds/dirtydarkness418
Summary: Future-Post 1x07 - Canon Divergent - Ten years after graduation, after acts of betrayal and a lifetime drowning in sin, Constance & St. Judes 2009 alumni come together for the 10 year weekend reunion where sex, lies and secrets combine for the art of seduction and the blurred lines of morale.





	High School Reunion

**Author's Note:**

> This is an intended multi-chap, but I've lost interest in it. So, unless I get a good handful of people who really want to see a continuation, this fic is abandoned indefinitely. I just thought I'd post since I did, after all, write it up. ;)
> 
> Also, this is just basically just one big fic of everybody having sex with everybody at their weekend ten-year high school reunion - though not at the same time. There is a tiny romantic thread between Chuck and Blair that comes to light later on, but smut w/ all the chars does dominate the majority of this (should I decide to continue it).

The cluster of attractive women hovered around Susie – the new secretary at Bass Industries – at her desk. Their breasts were practically grazing the top of Susie's head, and she knew then – more than she had in the past – how much she truly despised her genetics. Sure, she might be rather close in the attractive qualities of the other girls, but she was shorter than them, and so always squished beneath them, as they conjured up fantasies regarding themselves and their young, handsome boss.

In her own way, Susie decided this was her own fault. She had chosen to apply as the new secretary at Bass Industries. Her family connections with the Bass clan made it near impossible for them to refuse her. Her father and the ever-serious Mr. Bart Bass had been colleagues in their earlier days, so when she had been at a loss for any sort of work due to the economy for the last two years and frustrated to no end, her denial at taking the easy job at Bass Industries eventually had been ignored. The application had been placed in front of her for the hundredth time, except only this time she'd been aware of just a line to sign her name. Her father had filled out the rest. If she had thought clearly enough, she would have realized what had happened.

But she'd been so _tired_.

Sighing, she decided a bunch of large-breasted, shallow females was hardly a large price to pay for the great amount of money she received for working forty hours a week at Bass Industries.

The flashing red light and sound of her boss's voice broke through her thoughts. It also snapped the girls' attention from each other to everything surrounding the high-tech new black office phone.

"Miss Balance." He always referred to her by her formal name.

"Yes, Mr. Bass?" she replied, as professionally as she could.

Charles Bass hadn't really taken to her – another downside to her job. She didn't want that to affect how long she was working at the establishment, but it also confused her. As far as she could tell, and from what people told her and how men reacted to her presence, she was just as attractive as the other women in the office. Still, he remained almost impassive to her. She gathered that if he didn't have to talk to her, or look at her even, he wouldn't. She wondered if that was because she was the only brunette in the office.

"Send Kyle in," he said.

Her brows furrowed as the girls around her not so subtly gasped, thankfully beyond the sound range on the speaker phone.

"The new intern?" she asked, confused. He never concerned himself with interns. He left that to the blonde closest to her left, Jules.

The phone clicked, refusing any response Charles Bass would have spoken. She knew it was no accident. He somehow saw her as a lowly secretary, and he had little to no patience for those of her "station", though her family was hardly in the state of poverty. Just not to the level he was used to. She knew that for sure.

"Oh my god, I knew it," the redhead on her right said – Rebecca.

She closed her eyes, regretting immediately after her curiosity got the best of her, but she was too often in the dark when she chose to eavesdrop on the girls almost always surrounding her desk.

"What?"

Rebecca looked at her as if she was an unidentifiable creature she had no intention of interacting with.

She turned to look at Jules, and the girl behind her, Kara, who also said nothing.

"Nevermind," she muttered, opening a drawer to find the card listing all the interns' phone extensions.

"This is the third time this week," Jules deadpanned.

"You don't think…" Amanda behind her began.

"No, impossible," Rebecca confirmed, sounding sure of herself now. The rest looked at her. "He's experimental." She shrugged. "He's told us that." The slight confusion on the girls' faces made her continue. "Individually, and…through gossip."

Jules turned and leaned on the back of the overhanging counter on Susie's desk.

"Experimental is awful _nice_ , isn't it?"

"It's better than _gay_."

"Isn't he?"

" _No_. You saw the way he looked at Chloe the other day. He's still very much into women."

"Bi, then?"

 _He's clearly into everything…and everybody. Except me. Not that I mind_ , Susie thought, restraining herself from rolling her eyes. Not that any of them would notice.

"Hello, Kyle?" she said into the phone, this time keeping the device up to her ear so the girls wouldn't crowd so close. "Mr. Bass has asked to see you…You're welcome…I'll tell him." She pressed a button on the phone's base that transferred to Mr. Bass's office. "He'll be right in, Mr. Bass. Alright. I'll take my lunch." She hung up the phone and reached for her paper bag lunch beside her feet underneath the desk. She ignored the looks on the girls' faces until she got out of her chair and was around the desk.

"What?" she finally asked.

The girls' looked at each other in a way that clearly made fun of her.

Then Rebecca scoffed.

"You really don't know, do you?"

Susie's brows furrowed.

"He's going to sleep with him."

"Huh?"

The girls shared a look between each other again. She was getting sick of that.

"He does it every day with someone new," Rebecca continued.

"No repeats," Jules sighed.

Susie ignored her confusion and how appalled she was at the suggestion, also the anger she felt in herself for being so oblivious.

"Does he know?" she asked instead. She turned around as they all watched Kyle walk past them, knock lightly on Mr. Bass's door and walk in when granted permission.

"Judging from the looks of it," Rebecca said slyly, "he hasn't got a clue."

Susie gawked. "Is he even gay?" They said nothing. "Or bi?"

She shrugged. "I don't think it makes much difference. Chuck Bass gets what he wants…when he wants it."

 _Chuck_. _Was that what people he actually **liked** called him?_

The girls dispersed from around her desk, sparing her one last knowing glance. Uncomfortably, she headed for the door and made a quick exit. She would take a longer lunch today.

…

"The walls are soundproof," Chuck informed Kyle just after he'd turned to close the door. "Lock it," Chuck said.

Kyle looked confused, and slightly panicked.

"You're not in trouble," Chuck insisted. "I just don't want anyone overhearing us."

"But you said-"

Chuck gestured for him to lock the door again and Kyle did as he was told. Then he crossed the large office and sat in the plush chair across from Chuck's desk.

Chuck smiled, watching the fresh, young intern as he sunk into his chair. The boy – as he called him, even if he was of age – was as clueless as ever, and Chuck guessed he probably had a girlfriend. It was possible that he might have a wife, but there was no ring on his finger, so it seemed that was not the case.

Kyle was tall with sandy-blonde hair and blue eyes. He was lean and clearly fit, as was emphasized by the rolled-up sleeves on his vertical blue-lined slim button down shirt he wore and the loose zig-zag tie he wore around his neck. He was also modest, which Chuck would use to his advantage. Kyle was in his junior year at Yale and he was studying modern economics. It was only his first day at Bass Industries, so Chuck hadn't loaded on many tasks for him to do. What he was about to do now would be more than enough to send him home, feeling guilty and burdened, wondering if he could risk coming back the next day.

It was the test though. Chuck was proud of himself for having come up with such a clever one.

"So, you wanted to see me," he prompted, shaking Chuck out of the daze he'd fallen into.

Chuck smiled genuinely and put on his professional business face, even if just temporarily.

"How's your first day going, Kyle?" he asked, reclining farther back into his office chair and crossing his ankle over his knee. He folded his hands in his lap.

Kyle nodded with pursed lips, his straight blonde bangs swaying a little.

"So far so good," he said with a brilliant smile sprung straight from a smirk.

Chuck held his smile in check, using the fact that he had his planner and task sheets out before him on the desk to gaze across the space to Kyle's crotch and see how he was holding up. His eyes darkened even as they lowered to his papers because Kyle's dick was starting to make an entrance.

"I have here that you were supposed to arrange those files I had Judy lay out on your desk into chronological order and put them in the storage boxes in the back room." His eyes lifted up to Kyle's. "Is that right?"

His brows furrowed. "Isn't her name Susie? I don't think I've met a Judy here yet."

Chuck's smile was sympathetic and knowing. It took great effort to restrain from rolling his eyes, but seduction was all about playing the part and he was a great actor.

"Susie. That's right. Have you gotten to them?"

He sighed. "Not…completely. I got through about half, but then-"

"That's alright," Chuck cut in. "It's just your first day, and if you have any questions that Judy isn't able to answer-"

"Susie."

"-then you can just come and ask me. My door is always open."

"Except when it's locked," he countered lightly.

"You catch on fast," Chuck said, and winked. He opened the right-hand drawer on his desk and slipped in the papers he'd briefly read off of inside.

After he'd closed the drawer and looked up, he saw Kyle looking attentively at him, waiting for what he'd have to say next. It pleased him immensely, because everything was going as planned just like every time before.

"Now tell me, Kyle, do you have a girlfriend?" he asked smoothly.

Kyle's brows furrowed briefly but then he shook himself from the unexpected question.

"Uh, yeah," he chuckled. "I do. Her name's Mandy. We've been together since the 7th grade."

"How sweet," Chuck remarked. "Are your parents friends?"

He nodded. "Our grandparents too. It's kind of crazy how it all worked out."

Chuck kept his sentimental smile in place and reached for his cup of coffee, taking a sip.

"Think she's the one?" he inquired.

Kyle flushed briefly.

"Too soon to tell?" Chuck asked, his mood slightly dampened. It wasn't that he deliberately set out to break couples, but the forbidden rendezvous were always the more entertaining, exciting… _delicious_ ones to partake in.

Kyle swallowed. "I'm just not sure yet."

"Have you ever loved another girl?" he asked.

Kyle flushed again and then sat up, clearly starting to feel uncomfortable.

_Maybe he'd gone too far._

"Mr. Bass, I don't mean to be rude, but I'd really rather not go into any more detail about my personal life with a perfect stranger, even if it's my boss who I highly admire and respect."

"Perfect, huh?" Chuck asked smoothly, his teeth starting to show as his lips parted once more. "Admire…respect…I didn't realize you thought so highly of me, Mr. Devinson."

Kyle blinked and then his eyes widened in surprise.

"Oh, yes, I do, Mr. Bass. The only man I admire more is my own father."

Chuck smiled, straightened and leaned forward a little.

"Please, call me Chuck."

It took him a moment to react but finally he relaxed.

"Okay," he said, starting to smile like an over-excited schoolboy. "Chuck."

Chuck pushed himself up out of his chair and circled round the desk. Kyle watched him with a curious, expecting gaze, waiting for what he would do.

"Tell me, Kyle," Chuck began, leaning casually against the front of his desk. "Has college been a good experience for you?" Kyle blinked. "So far, I mean."

"Yeah…I guess. So far."

"Mm. And, have you done anything exciting?"

He laughed a little nervously, unnerved by his new boss's tone and where this might be going.

"I went whitewater rafting with my girlfriend up north a few weeks ago," he offered.

Chuck's sly smirk slowly spread into a Cheshire cat grin on his sickly perverted face.

"Whitewater rafting," he repeated. Kyle nodded in response. "Anything else?"

"Uh…"

"Anything," he pushed himself off his desk and crowded in on his new intern. "More…daring?"

Kyle's eyes widened. He could no longer ignore his boss's erection with how close he was. Right in his face. He couldn't deny his intentions either.

He sucked in a breath. "Mr. Bass…"

"Go ahead," he said huskily. "Touch it."

Kyle's eyes widened and he tried to scoot his chair away but Chuck held it in place.

"What's the matter, Kyle?" he purred, leaning over the chair and whispering into his ear. "Scared?"

He gulped. "I have a girlfriend, Mr. Bass."

"Chuck."

"I'd rather call you Mr. Bass."

Chuck stood back up straight and started to unbuckle his belt.

"Very well. I like a man who can be formal." He unzipped his pants and let them drop to the floor, stepping out of them.

"Mr. Bass," he swallowed. "This is sexual harassment."

He smirked. "Only if you don't enjoy the experience."

"I won't. I'm not!" He tried to scoot back again to no avail. Chuck's hands held tight to the arms on the chair and thus Kyle's position in it. There was no way for him to climb out and bolt for the door either. Chuck completely closed off access by standing directly in front of him.

"Give yourself a chance. College is a time for experimentation."

"Mr. Bass, please."

"Don't worry, I won't fire you," he sighed. "All I want is to get off." He pulled his dick out of his boxers and began to stroke it. Kyle's eyes widened and then he looked away, trying to erase the visual.

"I don't care. I don't do this. I'm not even gay."

"I'm not either."

"Then how can you be—"

"I experiment. Today feels like a guy week, and you, Mr. Devinson, have held my attention all morning." He turned the intern's head towards him by force. "Now go ahead. Suck me," he demanded.

Kyle shook his head, horrified.

"Do it," Chuck encouraged.

"You're going to fire me if I don't, aren't you?"

Chuck laughed. "Don't be ridiculous." He stroked his hair tenderly.

"You won't fire me?" he asked, looking up into his devilish eyes hesitantly.

Chuck smirked. "I won't have to. You're going to do it." Caught off-guard, Chuck forced Kyle's mouth on him, moving his head back and forth. At first the twenty-something year old resisted, pushing at his thighs to get away, but it grew on him, just as Chuck knew it would. Kyle wrapped his arms around Chuck's thighs, dug his fingers into his ass, and sucked with rapidity and what would seem to be enthusiasm.

Chuck groaned. "That's it." He laughed darkly. "I knew you'd enjoy this." He grabbed Kyle's head suddenly and held it still, beginning to thrust into his mouth and moaning loudly. Finally, he pulled himself free and reached around his desk for a button.

Kyle glanced up and was forced to look at the far wall as it lifted from the floor and behind it materialized a room with a king-sized bed inside it. His eyes widened and he looked back at Chuck, saliva dripping from his lips.

"Yes," Chuck said, not needing to be asked. "This is where I fuck all of you." Kyle looked back over to it. "Go."

Without hesitation, dazed at what was happening, Kyle stood up, his erection evident as he walked across the room and into the lavish – for a side office room – bedroom and dropped himself on the edge of the bed.

"Take your clothes off," Chuck instructed, as he himself continued to strip. "There's a pack of condoms in the end table drawer over there. Take one out."

Kyle swallowed, the consequences of what this would mean starting to weigh down on them.

"Don't think about it," Chuck said. "This won't ever happen again, and no one, not me or anyone in this office will spill our little secret."

Kyle spun around. "People in the office _know_?"

Chuck smirked, tossing his shirt to the side.

"They saw you walking in, didn't they?"

"Well, yes, but—"

"And I sent the secretary out to lunch just before you came in."

"So?"

"I only do that when I have…personal business to attend to."

Before Kyle could answer, Chuck came around the side of the bed and kissed him. Hard. Passionate. He was ruthless. Soon he was on top of him on the bed and sucking his intern's dick as if it was pure sugar and chocolate combined. He sucked and licked the long length of him as he squeezed his balls. Despite himself, the boy beneath him groaned, crying out at the pleasure in it. Chuck knew he wouldn't take initiative because the boy was, after all, mostly straight and tied to a female he intended to but probably wouldn't marry.

"Fuck," he cried out moments after Chuck had taken the condom from Kyle's sweaty hand and slid it on the length of him, thrusting into the tight hole in his ass. "Oh my god…oh my god."

"Oh yeah," Chuck grunted. "Fuck yeah," he growled, going faster. His hands were tight on Kyle's upheld knees and then his thighs. The tension was rising in him and creating euphoric experience.

He pulled out suddenly and rolled Kyle over.

"On your hands and knees," he ordered. "Oh, fuck yeah." He grabbed a hold of his ass and thrust into him again, evoking a cry from his newest intern. "You are fucking fantastic, Kyle. Fucking fantastic." When Kyle moved of his own accord back and forth along his dick, Chuck nearly lost it. He laughed, immensely enjoying the action. "Guess you aren't nearly as straight as you thought, Mr. Devinson."

The words sent Kyle over the edge.

"Oh my god…oh my god…I'm coming," he ground out, his head falling into the pillow in front of him.

"Oh, not yet, you're not." Chuck pounded harder, faster, into his tight little hole. Then he pulled out and came all over Kyle's back. Kyle rolled over and moved his hand up and down his dick as fast as it could go. Within seconds his sperm had shot up into the air and was then plastered along the side of his leg, the bed sheets and then the floor. When it was over, he laid his head back, closed his eyes and stilled his hand.

Chuck, his legs weak, but his smugness still fully intact, couldn't help but chuckle.

"There now, that wasn't so bad, was it?"

Kyle sighed, satisfaction clear on his face, and remorse soon after.

…

Susie returned to the office just in time to see the new intern, Kyle, looking somewhat disheveled, come out of Mr. Bass's office and head back to his little desk in the unforeseen corner where he'd been all morning. She stopped walking and her jaw dropped. The three women who'd swarmed around her desk before lunch were still there, smiling wide as their predictions were confirmed.

Susie walked back to the desk.

"Told you so," Jules informed her before she could get out a single word.

"I don't—"

The phone beeped.

"Miss Balanche."

She snapped out of her shock and quickly sat at her desk, quickly answering her boss's intercom call.

"Y-yes, Mr. Bass?"

"Did I get any messages while you were away?"

Her brows furrowed but the redhead tossed her a post-it note showing the single message that apparently had been delivered for the third time this week, according to the capital letters written above the top with exclamation points and underlining.

"J-just one," she said.

"Well?" he drawled, not nearly as snappy as he had been before. _Satisfied_. She cringed.

"Your sister called, a Miss Serena Van der Woodsen."

He sighed. "Pay it no heed."

"Uh-"

"That will be all, Miss Balanche."

Click.

She stared at the phone as she pressed the button and settled back into her chair. The girls looked at her expectantly, but she was in too much shock to vocalize what she was feeling about this new revelation proven to her right before her eyes.

"Why the hell did he hire me?" she muttered to herself, but the cluster of gossip girls had retreated to their desks.


End file.
